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Design of peptides that bind in the minor groove of DNA at 5'-(A,T)G(A,T)C(A,T)-3' sequences by a dimeric side-by-side motif
Abstract
The designed peptides pyridine-2-carboxamide-netropsin (2-PyN) and 1-methylimidazole-2-carboxamide-netropsin (2-ImN) are crescent-shaped synthetic analogs of the natural products netropsin (N) and distamycin A (D). Footprinting experiments indicate that the peptides 2-PyN and 2-ImN bind specifically the 5 base pair sequence 5'-TGTCA-3'. Affinity cleaving data suggest that the complexes, 2-ImN.5'-TGTCA-3' and 2-PyN.5'-TGTCA-3', are composed of two equivalent orientations which disfavor a 1:1 model. The footprinting and affinity cleaving data are in accord with a 2:1 complex where a novel side-by-side antiparallel dimer binds in the minor groove of double-helical DNA.
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Citations
Cited by
DNA minor-groove recognition by small molecules (up to 2000)
Neidle, S. (2001) · Natural Product Reports · doi:10.1039/a705982e · Cited by 494
Recognition of DNA by designed ligands at subnanomolar concentrations
Trauger, J. W., Baird, E. E., & Dervan, P. B. (1996) · Nature · doi:10.1038/382559a0 · Cited by 397
Self-citationSolid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids
Baird, E. E., & Dervan, P. B. (1996) · Journal of the American Chemical Society · doi:10.1021/ja960720z · Cited by 360
Self-citationA Structural Basis for Recognition of A·T and T·A Base Pairs in the Minor Groove of B-DNA
Kielkopf, C. L., White, S., Szewczyk, J. W., Turner, J. M., Baird, E. E., Dervan, P. B., & Rees, D. C. (1998) · Science · doi:10.1126/science.282.5386.111 · Cited by 306
Self-citationSequence-specific DNA recognition by polyamides
Dervan, P. B., & Bürli, R. W. (1999) · Current Opinion in Chemical Biology · doi:10.1016/s1367-5931(99)00027-7 · Cited by 283
Self-citationBailly, C., & Chaires, J. B. (1998) · Bioconjugate Chemistry · doi:10.1021/bc980008m · Cited by 254
DNA‐Binding Small Molecules as Inhibitors of Transcription Factors
Leung, C., Chan, D. S., Ma, V. P., & Ma, D. (2013) · Medicinal Research Reviews · doi:10.1002/med.21266 · Cited by 58
Metadata
- Authors
- Wade, W. S., Mrksich, M., & Dervan, P. B.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1992-11
- Volume
- 114
- Issue
- 23
- Pages
- 8783-8794
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1968614822
- Cited by
- 218
- References
- 0
- FWCI
- 1.78
- Type
- journal article
- Language
- en
- Open access
- closed
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